Turning a Conversation Into Valuable Content with BlueCat's Dana Iskoldski

Lindsay Tjepkema: Welcome to season six of the Casted podcast, and we're back with more of our very own customers. Why, might you ask? Well, because by becoming Casted customers, it's pretty clear how committed they are, not only to podcasting as a key piece of the future of their marketing efforts, but also the bigger picture of how these shows all fit into their integrated marketing strategy. They're the most forward- thinking brands that are harnessing the perspectives of experts with their podcasts. And then, they're not stopping there, they're ringing out those interviews to be amplified across all other marketing channels. They're practicing what we preach, and I want you to hear all about what they are doing, why they're doing it and how you can do it too. I'm Lindsay Tjepkema, CEO and co- founder of Casted, the first and only amplified marketing platform for B2B marketers, and this is our podcast. Today's conversation is with Dana Iskoldski, from BlueCat. As you know, IT can be a difficult industry to get people to talk about, especially in a B2B podcast, where organizations can be extra careful about what they can safely give away. Well, IT is exactly what BlueCat wanted to cover. So, they buckled down and thought hard about how they could create a community around their podcast, Network Disrupted, and how the show allowed them more flexibility than other traditional content, to turn a conversation into something lots of people would really find valuable. In the beginning, Dana was limited in what she could do, but the important thing was that she had a clear strategy about what the podcast should be about, who the ideal host would be, and how to get the most relevant guests to come on the show. Now with two seasons under her belt, Dana shares some of the most invaluable lessons that she's learned about how to best produce a podcast and keep leadership apprised of how and why it's successful. Dana, so glad that you're here. Thank you so much for joining us.

Dana Iskoldski: Thank you so much for having me, Lindsay.

Lindsay Tjepkema: All right. So, let's talk a little bit first about BlueCat and your show and how it came together, and the role that you play. Let's get oriented around that as we kick things off.

Dana Iskoldski: Sure. So, we launched our show in and about two years ago, before that I had just started working with BlueCat and it was in a PR meets a little bit of effort in brand awareness, kind of a role. And I remember podcasting, it was still kind of new to everyone. Maybe people listened to a podcast, my VP maybe had his NPR they listened to, and that was the one thing he did, and he didn't necessarily see how you could do a B2B tech podcast and make it successful. But we got to talking about... And this was between my VP of marketing, so his name's Jim, our chief strategy officer Andrew, who's just got a wealth of knowledge trapped in his head. And we got to talking about," Well, there's all these great stories that we hear around, Andrew's in a meeting and a customer of ours reveal something that would be so valuable for somebody else to hear, except no one was in the room." And it's really hard, especially in our industry where, I mean, we do very nerdy IT, that if it doesn't work, your organization might not function. And so, people keep that stuff really close to the chest or the vest or whatever you call it. So, getting someone after a call like that, to then come back with you and say," Hey, can we write up a case study? Or can we do a blog post with you again? Can we take another hour of your time?" It's really hard. And so, what we started thinking about was, well, how do we create... And we're all about building community, however you measure that or define that, and how do you allow people to make connections through content? And we realized, blogging might not necessarily be the best way. Podcasting gives you so much flexibility and it's still kind of new, you can do a lot with it. You can turn a conversation into something valuable for other people. So, that was the genesis of the podcast at BlueCat.

Lindsay Tjepkema: That's cool. Very cool. And your role there, I mean, as you've just told us, you were part of how it all came together and I know that you're running a lot still, so what do you do as far as the show? And I'm also curious, I'm always curious to ask this, what else do you do? Because it's very rare that somebody gets to focus on the show full- time, right? So, how does your role fit around this podcast and what are the different roles that you play within the show?

Dana Iskoldski: So, I'll start with the context, which is at the time that I started the podcast, I was mostly just responsible for our PR and our influence, our relationship strategy. It has since grown. So, I've recently taken over just like our content operation. This is very recent, I'm still learning the ropes, but I mean, there's obviously a very clear tie between podcasting and all of those things. And it's funny, when we started the directive was," We want a podcast." Right?" Figure it out."

Lindsay Tjepkema: Yeah.

Dana Iskoldski: And it really was a pet project. We didn't know how to measure it, so it wasn't like, it would count towards the exact same. It wouldn't count the exact same way as the stuff that I did before. So, it was really just one of those moon shoot, offshoot experiments that you do. And thankfully, I had the air cover to be able to spend the time on it and to be able to spend enough time on it. And as you know, it takes a lot. So, I did all of the concept design, the figuring out and hitting your head against a wall around," Okay, well, how much capacity do we have for this? Is this a weekly thing? Is that realistic? What's it about? Who's on it? What's the format?" Worked very closely with our host and well, BlueCat's Chief Strategy Officer, Andrew, to figure out where are the good topics? Who might be a great guest for something like this? And then, so from that design stage, I now produce the podcast. So, I don't host it, but I'll do everything from guest sourcing to arranging, making sure that we get all our editing done. At the very beginning, I started for a very little bit just editing the thing as well, quickly realized that is not in my wheelhouse of skills and hired someone to do that. I mean, first it was just a co- op on our team who happened to know GarageBand. And we would do a transcript of the episode. I would highlight the bits that I want to keep, send it to her, she would fix it up for me. Then she had to go back to school and I convinced her to stay on for a bit actually, and continue to do the editing. But after a while we realized, she's got to start a next internship. I need to find a freelancer for this. And so, I do the planning around it and the coordination, and I'm on all of the recording calls. So Lindsay, right now, it's you and me. In our version of this there's Andrew, the host, which would be you, the guest, which would be me, and then there's an extra person there, keeping an eye on the conversation and prompting it and helping figure out where can we go? And just monitoring, to make sure everything is working okay.

Lindsay Tjepkema: Yeah. That's awesome.

Dana Iskoldski: So, that's what I do now.

Lindsay Tjepkema: That's awesome.

Dana Iskoldski: And I'm in the midst of planning or rather, the early stages of planning, the third season here.

Lindsay Tjepkema: Got it. Man, I think that there's probably a lot of people listening that are really resonating with, first of all, all of the things you're doing and two, all the different parts of the process that are involved. Right?

Dana Iskoldski: Mm-hmm(affirmative).

Lindsay Tjepkema: So, let's talk a little bit about each of those stages, right? So, putting together your show, what's some of the advice that you would share around those questions that you just asked or shared that you would ask yourself? Like, what's the format like? Do we have guests? How do we find those guests? How did you start to answer those questions as you were, in your words, designing the show. How did you come to those? How did you really work out that strategy?

Dana Iskoldski: A lot of it had to do with... And creativity is bred through limitation, I guess, but we did not have much time or many resources to start off with this thing. There's some really great podcasts out there that are a huge production, both from an audio standpoint and from a storytelling perspective, where they've got interviews interspersed with voiceover narration, we could not do that. That would have been a huge lift. And so, we looked at, well, what is it that we can do? And what is it that we're good at? And we realized that what we're good at is one, teasing out information from other people and asking the right questions. And what we can manage is one- to- one interviews because they don't take as much prep as something like... Trying to think of the podcasts, I think Serial is probably a good example of the high production.

Lindsay Tjepkema: Yeah. Where there's lots of narratives and layers, and yeah.

Dana Iskoldski: Yeah. So, we did what we could, and that was the one- to- one interviews. They provide you... Especially when you've got a host who's a C- suite leader, who's traveling all over the world. I mean, not anymore.

Lindsay Tjepkema: Once upon a time.

Dana Iskoldski: But you need that flexibility and so, we chose the one- to- one interview format. We used to do prep sessions with guests ahead of time. We now realized you can almost just bucket the two meetings together. Our guests are usually representative of some of our buyers and some of our customers. So, we both know them well, and we end up generally knowing what they struggle with already, but they're also really good on the fly. A lot of them don't want to put too much prep into it anyway.

Lindsay Tjepkema: Yeah.

Dana Iskoldski: Does that answer the question?

Lindsay Tjepkema: Yeah. No, absolutely. So, that actually tees up next question. So, how do you find your guests? I know some people don't struggle with it at all and they're like," Oh my gosh, it's just no big deal." Others have more questions around it like," How do I know who to even go ask to be on the show?" How has that looked for you? How do you find your guests? How do you go ask the right people? What's that look like for you?

Dana Iskoldski: So, there's a type of guest that we have in mind when we're going after looking for guests and for us, it actually is really hard to land them, by the way. So, we look for again, people who represent the IT leaders that we talk to on a daily basis, whose struggles we're trying to pull up and shine some light on. So, it makes it easy from a, go on LinkedIn, search up the VP of IT, or the VP of architecture at a certain organization. That part's easy. The hard part comes where, and I don't know why, but the folks that we target their organizations often we find have some sort of policy around, that you need to go through an approval chain or don't say anything too sensitive. Don't get into the nitty- gritty of how you do things, because that's a risk.

Lindsay Tjepkema: Certain personas in certain industries, and certain verticals, are like that. They're more regulated. I mean, if you're going after for us, we're talking to marketers, right?

Dana Iskoldski: Yeah.

Lindsay Tjepkema: And this is literally what we do all the time, but you get into IT, you get into security, you get into science or medical device or legal. And all of those people, they either can or can't do it at all. And then, if they can, it's like," Okay, we need to have a script." Well, that kind of defeats the purpose." And we need to preview the questions first," and like, well, that's going to be really authentic. Or," We need to hear it before it goes live," which is, that can work. So yeah, again, I interrupted, but how does that work for you? How do you get around that?

Dana Iskoldski: So, it's funny that you talk about the Casted use case, because I used to work at a company that also marketed software to marketers. That was a whole nother world.

Lindsay Tjepkema: Yes.

Dana Iskoldski: And maybe it's because I'm on the PR end of BlueCat as well, I understand where the worry comes from with comms departments. And so, I've found, even when they review things, we send them the transcript up, as soon as we have it. I find, I haven't had many massive edits come in at all through the past two seasons that we've done. We once had a guest who asked us to remove something because she felt like it might reflect negatively on her organization because she revealed something that wasn't too great. But I dug in a little bit and was I like," Well, why are you worried? Is this something confidential? Or do you just feel like you're going to look bad?" And she actually said," You know what? You're right. Let's keep it in there. This is reality." And so, I find if you can get past the sort of blanket," No," and some organizations will have that, and it's just a policy that they have, and case closed there. But you can work with them, you'll send them the transcript in advance. You can send them the questions in advance. I don't mind putting together a set of dummy questions that may get used, may not get used. I think it's just about giving them a little bit more visibility into what they're signing up for. crosstalk.

Lindsay Tjepkema: Yeah. More comfort.

Dana Iskoldski: Yeah. But it is hard, especially to get the," Yes, we'll explore it." Definitely, leverage your network. If your executives or their past peers know someone. The best people to go to are people that you already trust and who already know you. Beyond that, you can do, and I've done cold LinkedIn outreach. You've got to send that a lot of messages to get responses back. Sometimes we've found gems. I think another really great thing to do is to look in the news and see who's already being interviewed, featured, whatever it is. You'll find that those people, if they're already there, their comms departments are most likely flexible. They clearly have an appetite for doing the personal brand building stuff. So, I've had success there as well, and you can find their emails online pretty easily.

Lindsay Tjepkema: Yeah. Okay. So you've talked about, you've mentioned your host, you have a C- suite host and it sounds like you guys work really well together. I'm assuming, based on how successful the show has been and everything that I'm hearing so far. How did you find the host? How did you select that? Was it just an obvious, like they're going to do it, or was there any discussion around what the show needed to be and therefore, who the show's host should be?

Dana Iskoldski: It was kind of obvious, it was partially built around him and because of the nature of his role and the kinds of interactions he has.

Lindsay Tjepkema: Natural thought leadership already.

Dana Iskoldski: Made it really easy. He was our lined up target from a marketing perspective or a brand building perspective, as the executive whose brand you're trying to build up.

Lindsay Tjepkema: Yeah. That makes sense. So, what advice do you have there for others who are in the shoes that you've been in and they're trying to build up their show and maybe it's not as obvious? Or maybe there's someone that everybody thinks it's obvious, but maybe that's not the best person for what you're trying to do with the show.

Dana Iskoldski: Be clear about what you want out of your show and I think that'll help you figure out who it is, who's a good fit. And then, consider things like are they bought in and are they willing to give you the time? It's not just, show up for the recording and be done with it, especially when you're starting it up. You also want their input, you want their feedback. So, find someone who is excited about it and is an advocate. You can always tweak it a little bit. Like if you've got someone who's really willing and is capable and can speak in a podcast form, they've got to be a little bit engaging and interesting and open to learning new techniques for pulling things out of people, or whatever the format of your podcast is. I guess, look for all those things and whoever's score is the highest on that matrix is your target, and work as closely as you can with them, but try to do as much legwork as possible for them.

Lindsay Tjepkema: That makes sense. So again, you have someone who's a C- level executive, this is not what he's spending all of his time doing. This is not what he should be spending all of his time doing. How do you help manage that time? Do you have any advice that you can give? Because that's something I hear a lot, as far as like," Oh, it should definitely be our CMO, it should definitely be our, this person, that person, this person, but he or she is very concerned about how much time it's going to take." Because, it does take time, like you said, it isn't just showing up for interviews, but there are lots of different ways, I've heard about clumping all the interviews together at a certain time of the week or month or whatever. Others is, trying to minimize the work over here. What do you do to help manage that time and also, keep him engaged when his calendar inevitably, I'm sure gets insane, and he still has his podcast to do?

Dana Iskoldski: Yeah. So, the one tip and it might not be super relevant to exactly this question, but is, make friends with the executive assistant who works with them. They're going to help you a lot and give you insight into either how they feel about something or whether they're too busy or what's coming down the pipeline for them. So, do that, but then second, do as much research as you can for them. So, say you've got a guest and maybe you've done the outreach, and the guest is ready to meet your host, prep your host, give them all of the information. We use Slack at BlueCat. So, I literally just send a whole bullet point list of," Here's what you should know. Here's what I think you could ask the person about, based on what I know." And I send that, I mean, our host is pretty good, so he doesn't need much time and he can do things on the fly. Some people like to get this material further in advance.

Lindsay Tjepkema: crosstalk prep.

Dana Iskoldski: So, figure out your host's style, but just as much research as you can, put it all, centralize it in front of them and then give them... I don't know if you want to start scheduling maybe like 10 minutes ahead of the call or something like that, to just give them the time to breathe if they haven't yet, and do some just basic Googling or look at the person's LinkedIn that they're about to interview, I find that helps. And then, take ownership of the thing. Don't ask too much about," What should we keep? What should we cut?" You should know the content well enough too, that the editing process is very light on them.

Lindsay Tjepkema: Yeah. Okay. So, you've proven that you are an incredibly thorough producer. I mean, I think that, that's very clear. I think people are probably taking notes like," Oh my gosh, that's a good idea. Oh, that's a really good idea, too." What do you think it is about you, what skills do you have that you think are important for a role like yours? To producing a show, to keeping it on track, to keeping it organized, to keeping the host prepared and confident and managing their time? What do you think is important if you are going to be the person behind the scenes of a show?

Dana Iskoldski: Okay. Therapy session. I think to some degree, you need to be detail- oriented because there's so many little things that rely on one another within the setting up of the podcast. And you can very easily start to feel a little bit over your head or in over your head about it. And then, the other thing is just the ability to go with the flow, because as much prep as you do, things will not go according to plan and you need to be okay with that. You can draft as many questions as you want for your host, they're not going to follow the script. And it's probably best that they-

Lindsay Tjepkema: Hopefully they don't follow the script.

Dana Iskoldski: Exactly.

Lindsay Tjepkema: That's when you get the good stuff. Yeah.

Dana Iskoldski: Yeah. The whole point, I think in doing the prep and being so prepared, is just to be able to be a little bit more flexible on the fly. So, I guess it's a mix of those things. And then, if you've got an eye for content or you've got... I feel like it's easy to fall into the platitudes of content and reiterate the same things that everyone else says. If you can look past that and both push your host and push your guests, and set the expectation up front, that we're here to deliver value to the listener. If that means I need you to get a little uncomfortable and tell me a specific story of how you did something, please do. And so, it's to be able to see that, I think, maybe everyone's got that eye, maybe not everyone does, but I think that makes a podcast great.

Lindsay Tjepkema: We've talked about how your show came together, a little bit about how you make it tick. What do you do with it once you have an episode? So, you go through all this work, you have a great guest, your host is prepared. You're doing all of this crazy, amazing organization in the background to make it happen. And as we talked about, one of the things you said, right before we hit record, was you can't just send something out to Spotify and hope that it's going to get a million listens, especially in B2B, because... And this is one thing that I talked to a lot of people about, is that B2C or just consumer podcasts, somebody is on Spotify and Apple looking for true crime podcasts or whatever it is. Whereas B2B, you're hoping that people find your content based on search intent. Like," I want to learn this, I want to buy this. I want to dive deeper into this, so I'm going to search for it and hopefully this content comes up, one of the pieces of content is a show." So, let's talk a little bit about what you do once you have a show and how you get it out there into the world, and what else you do with it.

Dana Iskoldski: Yeah, sure. So, I think probably important to note is having someone listen to your podcast is great. That's not the only value you get out of a podcast. I think for us, especially when we came out, it was amazing if someone listens through all the way to the end. If someone even just knows though, that the podcast exists and can tie the name of our host to the name of the podcast, and maybe there's a guest there who's super relevant and someone identifies with, even if they don't listen to the thing, that's success to us. So, the high level, I guess you can look at impressions here, but obviously do the whole social sharing, that's kind of the obvious thing. Don't assume that the algorithms are helping you, and get comfortable reposting things a lot, and creating a cadence where you've got this new... And this is a content problem in general is distribution, and how to do that right and make the most of the content piece you just invested time into. Create a cadence where you've got your podcast. Well, what do you turn that into? Do you turn it into, here's an announcement post, but then, pull some stats or some facts out of it for the week after and then, the week after that, and the week after that. So, create a bit of a drip. Use your other available channels to your advantage. So, if you've got email, if your host knows people, do that. The other thing that we do is we turn our podcast episodes into blogs as well. So, we repurpose content in a bunch of ways. We turn our episodes into these little PowerPoints as well, that we post on social, as little summaries, but not everyone's an audio listener and that's okay. And if you feel like you can meet people where they're at, and I know this takes time, summarizing a blog episode is not a one hour affair... Summarizing a podcast episode is not a one hour affair, but if you can invest the time there, then you've got another excuse to share it, and another excuse to interact with your guest. On the guest front, I find many people just hope that the guest will share. And again, not an expectation on guests to be sharing at all, but I think if you're inviting people onto your podcast, you've got at least a sense that the community is important and the value of the network and the amplification that the guest brings exists. This is not my idea, I actually stole it off of somebody else's podcast is, create a little fact sheet for your guests after the fact, that's almost got all the materials that they're going to need to either send to their comms teams, who by the way, love this stuff, and want to share from their corporate account. It's a great employer brand thing for them, but also for your guest. So, I remember the fact sheet that I had included the links to everything, both the podcast episode, the blog, when it comes out, all the socials that are relevant, a couple of sample posts that they could literally copy/ paste right into their LinkedIn or Twitter, and even some imagery that they could literally swipe.

Lindsay Tjepkema: Yeah. Just making it super, super easy. I know when people do that, for me, it's like," Oh, okay, well I'll just take this and I'll personalize it a little bit." But giving somebody something to start with, they're going to be that much more likely. I think even people with the best intentions who might love you, love your show, love everything about the experience that they had, people are busy. So, the easier, the fewer barriers that they have to scale, the better, and the more likely they're going to take what you have and share it. Okay. So, in summary, looking at how your show has come together and you've told me you're starting to work on season three, right? That's coming down the pipe. So, you're a couple of seasons in, what overall, lessons learned, do you wish you had known... What you wish you had known then, what you know now, what would you share to others that are either looking to get started or scale up their podcasting efforts?

Dana Iskoldski: I would say that it takes a long time and you're not going to feel a lot of what success or what you think success is going to feel like, for a long time. So, set yourself little milestones or little wins, whether it's just making it to publishing the first episode or getting the first person to comment on one of your social posts, where you shared it out saying," I thought this was great. I listened to it." You're not going to see that in the numbers yet, necessarily, but that means so much, when a real human being took the time to comment something like that. So, progress is slow. Don't assume that it's going to be a smash hit right away. Make sure that you give distribution some solid thought, even though I know you've probably already put a lot of time into doing something. And hope that you have enough, I guess, time to put into it, because these things do take a lot of effort. I think one thing that content in general suffers from is the assumption that it's so easy. It's just a blog post.

Lindsay Tjepkema: Oh my gosh, yes.

Dana Iskoldski: It's," Why don't I spin up a blog? Why don't I start a podcast?" It takes a lot more work and just go into it eyes wide open, so that you're not surprised or you don't end up having to go back on a commitment that you made later.

Lindsay Tjepkema: Yeah, for sure. Yep. I love your thought there about the steps along the way, like celebrating the small wins and small victories, because it is, it is a marathon, it's not a sprint, but that doesn't mean that you have to delay all gratification until you hit a million listeners or have direct attribution of however much dollars in revenue. There are victories along the way, like you said, there's publishing the first show. There's getting your first unsolicited feedback or review. There's reaching some milestones of small listeners. Like," We had our first 10 listeners. We had our first show that had 100 listeners in the first week." I mean, those things are things to celebrate because they are showing that momentum is accelerating, and that's what you want, is continued listenership. You want people that are coming back, you want new people being added all the time, and you want to start to get feedback from internal and external about how it's going and what people think.

Dana Iskoldski: Yeah. And don't be afraid to educate people on what a podcast is and how it works, is the next thing, like these little wins, you might understand what they mean, keep translating them for the rest of your peers.

Lindsay Tjepkema: That's so important for your peers and also for your leadership, setting expectations around," This is why we're doing this and this is what success looks like in our first month, in our first year." Because even the leaders with the best of intentions like," Hey, we need to go start a podcast. I believe in it. I'm a big fan," might think something is possible, that's not. Because like you said, content is perceived to be, oh so easy, just go start a podcast. Right? I keep hearing about how anybody can do it. Well, okay, just because you can, doesn't mean it's going to be great. Right? And there's a lot of effort that goes into greatness and there's a lot of time and there's a lot of, like we said, small victories along the way. So, I think that's super important, is making sure you're educating internally like," Hey, this is what we're doing. This is why we're doing it. This is what we expect to see." Super important.

Dana Iskoldski: I mean, I can say, I did not have a definition of success for a year out. I was taking it week- by- week. Thankfully, I had the air cover to be able to do that. So, if you've got leadership that allows for that experimentation, take the opportunity, so that you can at least learn what success might look like down the road.

Lindsay Tjepkema: Yeah. And that's important too, you had that awareness of," We don't know." Right?" This is a test." I think that's important too. Even if you say," I don't know what success looks like, but we're going to try this and here's these other things that we're going to continue doing that are a little bit more tried and true." Yeah. It's really important going into it. Awesome.

Dana Iskoldski: This is an awesome podcast.

Lindsay Tjepkema: Yeah. And so, you said season three is coming up maybe in the fall or so, depending on how many people are listening, where can they find it, in the meantime?

Dana Iskoldski: They can find it at networkdisrupted. com, which actually redirects to a Casted sub- domain.

Lindsay Tjepkema: Very nice.

Dana Iskoldski: So, thanks for hosting that. Or, Network Disrupted on Twitter and LinkedIn.

Lindsay Tjepkema: Awesome. Well, Dana, thank you so much for being here and for sharing the behind the scenes learnings that you have collected at BlueCat.

Dana Iskoldski: Of course, thanks for having me on.

Lindsay Tjepkema: That's our show. Thanks so much for listening, and for more from today's guest and some pretty amazing content that they've inspired, visit casted. us, and be sure to subscribe to our newsletter, to get the latest on all things amplified marketing, B2B podcasting, and a lot more.